Simmons attended St. Rita High School on Chicago's south side. In 1993, he was named Chicago Sun-Times Prep Athlete of the Year for his participation in both football and track. As a senior, Simmons won the state championship in the 100- and 200-meter dash events with times of 10.5 seconds and 21.58 seconds, respectively. He shares a distinction with two other NFL players who also attended both St. Rita and the University of Wisconsin–Madison: former high school and college teammate Ahmad Merritt, and former Chicago BearDennis Lick. Simmons and Merritt played against each other and caught touchdown passes in World Bowl IX. In April 2011, Simmons was inducted into the St. Rita High School Hall of Fame.
College career
Simmons played college football at the University of Wisconsin–Madison. He left Wisconsin as the school's all-time leader in touchdown receptions with 23, earning him the nickname "Touchdown Tony" among the Camp Randall faithful. He also competed in track Wisconsin and he is a Big Ten 100m and 200m Champion. He was part of the 1995-1997 Triple Crown Champions
NFL career
Simmons was drafted into the NFL in the second round of the 1998 NFL Draft by the New England Patriots. Simmons played five seasons as a pro with the New England Patriots, Cleveland Browns, Indianapolis Colts and New York Giants. He amassed 58 receptions for 998 yards with six touchdowns, averaging 20.8 receiving yards per game. Simmons also had 12 punt/kick returns for 241 yards, averaging 20.1 yards per return.
NFL Europe career
In 2001, Simmons starred at wide receiver for the regular-season champion Barcelona Dragons of NFL Europa. He finished the season with 32 catches for 538 yards and caught seven touchdowns.
Simmons played from 2004 to 2007 for CFL teams Edmonton Eskimos, and BC Lions as a wide receiver. He recorded 34 receptions for 504 yards, averaging 14.8 yards with four touchdowns. BC Lions reached and won the Prestigious 94th Grey Cup.
Career in Europe and Asia
Denmark
In March 2010, Simmons signed with Danish team Triangle Razorbacks. He played wide receiver and served as the team's offensive coordinator and special-teams coach. Played in the Mermaid Bowl and finished 2nd place.
Hungary
In January 2011, Simmons joined the Hungarian team Békéscsaba Raptors as head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator, strength/speed coach and wide receiver. The team reached the Hungarian Football League Pannon Bowl and finished 2nd place.
India
In January 2012, Simmons joined the EFLIElite Football of India to help develop coaches and players as a coaching consultant, coach and referee in the first-ever American football played in India. He also served as offensive coordinator, defensive coordinator, special-teams coordinator, strength/speed coach and referee.
Austria
In April 2012, Simmons joined the Austrian team Amstetten Thunder as head coach, offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.
Italy
In January 2013, Simmons joined the Italian team Cagliari Crusaders as head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.
Brazil
In July 2013, Simmons joined the Brazilian team East São Paulo as head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.
Finland
In November 2013, Simmons agreed to a deal with the Kouvola Indians to serve as their head coach for the 2014 Maple League season. He also served as offensive coordinator, defensive coordinator, special-teams coordinator, strength/speed coach and coaching consultant.
Italy
In January 2015, Simmons joined the Briganti Napoli to serve as their head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.
In January 2016, Simmons joined the Warsaw Sharks as head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.
Russia
In May 2016, Simmons joined the Moscow Patriots as head coach. He also served as offensive coordinator, coaching consultant, special-teams coordinator and strength/speed coach. The Moscow Patriots won the Russian American Football Championship with a perfect season. Also, the head coach, coaching consultant, offensive coordinator and strength/speed coach for the Russian National American Football Team.
Brazil
In October 2016, Simmons joined the Sao Paulo Spartans as head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.
Switzerland
In January 2017, Simmons joined the Lausanne LUCAF Owls as head coach. He also served as offensive coordinator, defensive coordinator, special-teams coordinator and strength/speed coach.